2-[(3-fluorophenyl)(hydroxy)methyl]-4-methoxy-N-methylbenzamide → 2-(3-fluorobenzyl)-4-methoxy-N-methylbenzamide

HRID 2196386Notes

Reaction equation

HRID 2196386 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8](O)[C:9]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:10]=2[C:11]([NH:13][CH3:14])=[O:12])[CH:5]=[CH:6][CH:7]=1>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][C:9]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:10]=1[C:11]([NH:13][CH3:14])=[O:12]

Participants

4

Reactant 1

HCID 685140052-[(3-fluorophenyl)(hydroxy)methyl]-4-methoxy-N-methylbenzamide

Product 1

HCID 685098412-(3-fluorobenzyl)-4-methoxy-N-methylbenzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-[(3-fluorophenyl)(hydroxy)methyl]-4-methoxy-N-methylbenzamide (500 mg) in methanol was added 500 mg of Pd/C (10%). The reaction was stirred overnight under H2 (1 atm), then filtered through celite and concentrated to give 2-(3-fluorobenzyl)-4-methoxy-N-methylbenzamide, which was used without further purification.

Workup

  1. filtrationfiltered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-38d13476ecb34b5898155473be087420
Source dataset
uspto-grants-2012_12
Patent number
US08338449B2

Reaction notes

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